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I’m a Lakers fan. And it has been tough to watch Kobe for the last few years. First, the Achilles. Then the knee. After that, the shoulder. This year, #119 of 119 (through December 1) in shooting percentage. While it may be heresy inside the
Staples Center, Kobe should have retired several years ago and gone out on top. Instead, I’ll always remember him going 4 for 20 (including an airball with 7 seconds left) on the night he announced his retirement. Will his legacy be tarnished? Probably.

Kobe reminds me of Steve Carlton, the Hall of Fame pitcher for the St. Louis Cardinals and Philadelphia Phillies while I was growing up. “Lefty” was a 10 time All-Star and won four Cy Young awards. But, at the end of his career, Carlton was pitching in middle relief with ERAs that you’d expect out of Little Leaguers, not future Hall of Famers.

Carlton should have retired after his injury riddled 1985 season, and not trudged out to the mound for the Giants, White Sox, Indians, and Twins before he ultimately retired after 1988 (actually, he tried to get a job for the 1989 season too, but couldn’t find a team to take him). Almost 30 years have gone by, and I still remember Carlton warming up in the Minnesota bullpen with a 6+ ERA.

Both Kobe and Lefty waited too long to leave their sports. They should have gone out on top; not waited until fans were snickering under their breaths.

OAKLAND, CA - NOVEMBER 24: Kobe Bryant #24 of the Los Angeles Lakers looks on while there's a break during the game against against the Golden State Warriors at ORACLE Arena on November 24, 2015 in Oakland, California.

If you are a business owner evaluating your options for your own company, don’t make the same mistake! You should take note of these magnificent downfalls, and consider the possible impact of waiting too long to take your own victory lap.

Realistically, business owners have the same problem that Kobe and Lefty had. Bryant and Carlton had enormous egos – it’s what made them who they were. No one works harder than Kobe does. Kobe expects to be the best, and for most of his career, really was. Carlton wanted to win the strikeout duel with Nolan Ryan. Unfortunately, both of their bodies gave out (and Nolan Ryan pitched effectively to the ripe old age of 46).

Business owners have similar egos. If they didn’t, their businesses most likely wouldn’t have developed to be successful companies that are being targeted for acquisition. But, since business owners tend not to suffer career ending knee or elbow injuries, it’s harder for them to be forced to make a decision to not leave too late.

Like Kobe reaching for another championship or Lefty looking for a few more strikeouts, in working with middle market entrepreneurs considering exits from their companies, I regularly hear the following: “I don’t want to leave money on the table. If I just wait one more year, my business is going to grow, and I’ll be able to sell it for a lot more than I can sell it for today.”

But, what I never hear is: “My personal wealth is concentrated in my business and there is a long list of business risks that could make my company much less attractive than it is now and prevent me from selling my company at all a year from now, or at least not at the same attractive price I can get today.”

Ego prevents thoughts of failure. But there are risks that risks your greatest asset. For example, here are a few things to consider as you are trying to make a decision:

Is your company dependent on key employees or vendors that you don’t control? I recently advised a company that ultimately decided not to complete a transaction. Soon after making the decision, two key employees left the company and took a number of key customers with them as they opened up a competitor.

What happens if your customers change direction? Companies with a track record of growth attract buyers. Companies that shrank last year don’t.

Could outside factors impact your market? For example, look at the regulatory changes surrounding health care in the last few years. Buyers hate risk. If next year brings on more risk, you’ll wish you had already sold.

What if the market changes? In 2005 and 2006, the M&A market was flying high. By 2008, business sales had dropped to virtually zero. We’ve been at a peak in the market for the last two years. What happens if uncertainty arises due to next year’s presidential election?

Waiting can be the right choice. But, remember, there is downside risk as well as upside opportunity.